7,12-dimethylbenzo ( a ) anthracene

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Structural formula
Structural formula of 7,12-dimethylbenzo [a] anthracene
General
Surname 7,12-dimethylbenzo [ a ] anthracene
other names
  • 7,12-dimethylbenz [ a ] anthracene
  • 7,12-dimethyl-1,2-benzanthracene
  • 9,10-dimethyl-1,2-benzanthracene
  • DMBA
Molecular formula C 20 H 16
Brief description

yellow solid with a sour odor

External identifiers / databases
CAS number 57-97-6
EC number 200-359-5
ECHA InfoCard 100,000,326
PubChem 6001
Wikidata Q187487
properties
Molar mass 256.35  g · mol -1
Physical state

firmly

Melting point

122-123 ° C 

solubility
safety instructions
GHS labeling of hazardous substances
08 - Dangerous to health 07 - Warning

danger

H and P phrases H: 302-350
P: 201-308 + 313
MAK

not classified, as a suspected carcinogenic effect

Toxicological data

327 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

7,12-Dimethylbenzo [ a ] anthracene , usually abbreviated as DMBA , is a polycyclic aromatic hydrocarbon (PAH). The basic substance of the compound is benzo [ a ] anthracene . DMBA is highly carcinogenic , one of the most potent carcinogens and one of the most powerful polycyclic aromatic hydrocarbons to cause cancer.

It is used in oncology to trigger tumors in model organisms .

properties

DMBA forms greenish-yellow crystals that melt at 122.5 ° C. It is extremely poorly soluble in water. Only 0.055 mg dissolve in one liter of water at 24 ° C. The octanol-water partition coefficient (log K) is 5.70. DMBA is very soluble in acetone as well as in benzene .

use

Due to its strong carcinogenic effect, there is no technical application for DMBA. In oncology it is a standard carcinogen that is frequently used to produce malignant tumors in model organisms .

DMBA is broken down in the organism by the P450 enzymes to metabolites that form adducts with the DNA .

Skin cancer or breast cancer can be produced in the model organisms, depending on the form of application . Leukemia and tumors can also be induced in other organs.

Discovery story

DMBA was first synthesized in 1938 by WE Bachmann and JM Chemerda. The carcinogenic potency of DMBA was also discovered in the same year by WE Bachmann and colleagues at the University of Michigan . They found that DMBA induces tumors twice as quickly as 3-methylcholanthrene in mice . With variations on the benzo [ a ] anthracene base, they were able to see that the 7,12 position of the methyl groups is responsible for a high level of carcinogenicity.

literature

  • LW Chow et al .: A rat cell line derived from DMBA-induced mammary carcinoma. In: Life Sciences 73, 2003, pp. 27-40.
  • T. Ishikawa et al: Inhibition of skin cancer by IP6 in vivo: initiation-promotion model. In: Anticancer Research 19, 1999, pp. 3749-3752.
  • HE Kleiner et al .: Role of cytochrome p4501 family members in the metabolic activation of polycyclic aromatic hydrocarbons in mouse epidermis. In: Chemical Research in Toxicology 17, 2004, pp. 1667-1674.
  • E. Boyland: The history and future of chemical carcinogenesis. In: British Medical Bulletin 36, 1980, pp. 5-10; PMID 7020830 (Review)

Individual evidence

  1. ↑ a b c d e f Entry on 7,12-dimethylbenz (a) anthracene in the GESTIS substance database of the IFA , accessed on March 28, 2019(JavaScript required) .
  2. ↑ a b c Entry on 7,12-dimethylbenzo [a] anthracene. In: Römpp Online . Georg Thieme Verlag, accessed on September 16, 2011.
  3. ↑ MM Coombs and TS Bhatt: Cyclopenta (a) phenanthrenes. CUP Archive, 1987, p. 8. ISBN 0-521-30123-8 .
  4. ↑ EL Cavalieri et al .: Comparative dose-response tumorigenicity studies of dibenzo [a, l] pyrene versus 7,12-dimethylbenz [a] anthracene, benzo [a] pyrene and two dibenzo [a, l] pyrene dihydrodiols in mouse skin and rat mammary gland. In: Carcinogenesis 12, 1991, pp. 1939-1944; PMID 1934274 .
  5. ↑ a b David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-192.
  6. ↑ SH Yalkowsky and RM Dannenfelser: The AQUASOL Database of Aqueous Solubility. 5th edition, College of Pharmacy, 1992.
  7. ↑ C. Hansch et al: Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. American Chemical Society, 1995, p. 166.
  8. ↑ PD Devanesan et al .: Identification and quantitation of 7,12-dimethylbenz [a] anthracene-DNA adducts formed in mouse skin. In: Chemical Research in Toxicology 6, 1993, pp. 364-371; PMID 7686408 .
  9. ↑ NV RamaKrishna et al.: Mechanism of metabolic activation of the potent carcinogen 7,12-dimethylbenz [a] anthracene. In: Chemical Research in Toxicology 5, 1992, pp. 220-226, PMID 1643251 .
  10. ↑ SS Bhattacharyya et al: A synthetic coumarin (4-methyl-7 hydroxy coumarin) has anti-cancer potentials against DMBA-induced skin cancer in mice. In: European Journal of Pharmacology . April 2009, PMID 19393233
  11. ↑ H. Bartsch et al .: Chronic exposure to a GSM-like signal (mobile phone) does not stimulate the development of DMBA-induced mammary tumors in rats: results of three consecutive studies. In: Radiation Research 157, 2002, pp. 183-190, PMID 11835682 (review).
  12. ↑ T. Sugiyama et al .: 7,12-DMBA-induced rat leukemia: a review with insights into future research. In: Leukemia Research 26, 2002, pp. 1053-1068, PMID 12443876 .
  13. ↑ WE Bachmann and JM Chemerda: The synthesis of 9,10-dimethyl-1: 2-benzanthracene, 9,10-diethyl-1: 2-benzanthracene and 5,9,10-trimethyl-1: 2-benzanthracene. In: Journal of the American Chemical Society 60, 1938, p. 1023.
  14. ^ WE Bachmann et al .: The rapid production of tumors by two new hydrocarbons. In: Yale J Biol Med. 11, 1938, pp. 97-102, PMC 2601969 (free full text).
  15. ^ WE Bachmann et al .: The rapid production of tumors by two new hydrocarbons. In: Yale J Biol Med. 73, 1939, pp. 259-263, PMID 11765945 .